10 things I wish I’d known before I chose freelancing

Like many young people working in the world today, I was a freelancer. I freelanced for a solid two years after graduating from film school. It was exhilarating and an exciting way to jump right into working in the industry that I loved the most. However after some time living the freelance life, I realized that there are some serious drawbacks that I wished I had been aware of before diving in.

1. You don’t really have days off.

One of the first things I learned when I started my freelance journey, is that you don’t have days off the way you might think you would. Sure, choosing your own hours or taking on the jobs of your choosing, might make it seem like you can also choose your off hours too, but that isn’t really the case. Since no work is guaranteed you might find yourself with a couple free days in a row, but unless you’ve planned for them and saved up a comfortable amount of money, you will probably find yourself spending your free days trying to drum up more work. It might not sound like a lot, but answering emails, making calls, and posting on job boards in your spare time is almost a job in itself. Also, since your time is unstructured, in your off-hours it’s easy to feel pressure to be always looking for work. The way I learned to combat this was by trying to set a schedule for myself on my off-days. If I found myself with free time Monday-Friday between 9 a.m. and 5 p.m., I’d work on getting more work. But, once 5 p.m. hit I’d mentally clock out. Working ’round the clock isn’t good for you, and you’ve gotta protect that mental health.


2. Your schedule will be a little whack.

Something I thought I understood, but didn’t really understand until I was a working freelancer, is that your schedule will be a little crazy. Especially when you’re starting out and trying to make a name for yourself, most of your work will be secured at the last second. Working in film I’d find myself getting a text at 9 p.m. the night before a gig, asking if I wanted to work the next morning, and I’d have to say yes because I needed the money and the experience. The result is it might become very hard for you to plan non-work activities more than a few days in advance. I can’t tell you how many times I’ve had to bail on friends or family because a last-second job was offered to me that I needed to take. The upside is that it forces you to be flexible and creative with your time (hello laundromat in the middle of a Tuesday afternoon), and to live more spur of the moment (you’re way more likely to accept a last second dinner invite from your friend if you haven’t had a chance to see her in weeks). The downside is that you might miss having a calendar that belongs to you and you alone.

3. Your lifestyle might hurt the people you love.

The toughest part of freelancing for me was balancing my crazy schedule with the people I love. Having very little to no control over your schedule puts you in a position of having to let people down from time to time. If you have to do that a few times in a row, their patience might start to wear a little a thin, despite everyone’s best intentions. This is especially true if you have friends, family, or a partner that doesn’t freelance as they might not totally relate to your struggle. Even worse, holidays are often when new freelancers are in the highest demand since most people don’t want to work over holidays if they can help it. Here I found the key was balance. There were certain events that I would write in my calendar in pen, and regardless of what job was offered to me I’d make sure I didn’t budge. On the other hand, there were instances where I knew I had to strategically miss out on an important activity because the professional opportunity was too good to pass up, and I’d have to just hope the person would understand.

4. You need to know your rights.

One of the downsides of freelancing is since you’re often the “new kid” on every job you take, you don’t have the benefit of a company or a team of coworkers to protect you from situations where you might be in danger of being taken advantage of. One of my biggest recommendations is to read every contract before you sign it and make sure you’re okay with everything it says. Yes, contracts can be tedious, but important stuff like when the employer plans on paying you, and any rules you shouldn’t break are usually outlined in them, so it’s good to be aware of what they say. Always save and file all your paperwork in case you need it later. Be mindful if you are working too many hours in a row, and what the labor laws in your city are. If you work in a freelance industry like graphic design or photography where you’re creating a “product,” be sure to have contracts and steps in place that dictate when you hand over the work to the client and how it can be used. Of course we want to think the best of everyone, but it is important to remember that in freelancing you are your own HR department, and you’ve got to take care of yourself.

5. You are your own product and you’re always networking.

One of the hardest things for me to get used to as a card-carrying shy person, was that even when you’re on the job you’re selling yourself. Your demeanor, how you work with others, and your friendliness are all your keys to getting hired for the next job. I struggled with this for a while because I’m someone who needs to focus when I’m working, and I have a really hard time being able to balance being light and friendly while I’m thinking or accomplishing a task. What I’ve learned is that the finished product is only part of the job. The other part — being kind, friendly, and interested in the lives of the people you’re working with — goes a long way toward securing your next job. Another thing to keep in mind is your internet presence. It’s really helpful to have a site where all your work is housed so you can point prospective employers to it.

6. Last month’s work is this week’s paycheck.

Something I didn’t realize about freelancing until I was in it, is that every company or person you work for is going to have a different payment schedule, and it usually isn’t right away. You will probably have to wait some time for your paychecks to show up, so it’s very important to remember that the work you did last month pays for the month you’re currently in, and so on. If you can’t get on that kind of money schedule it will be a struggle come rent time.


7. You might get judgment from people who don’t know better.

My freelancer friends and I would often joke that it was always impossible to explain our job to people like parents or grandparents, as the idea of freelancing is still relatively new to many. The downside to this is that some people in your life might not see your freelancing as a career, and worse they might treat your career as less than because it is not the traditional 9-5 model they are used to. In cases like this it’s important to remember to have confidence in yourself and your career no matter what. Even if people don’t understand what you do, it doesn’t take away the validity of the career and the life you’ve chosen for yourself.

8. Company benefits can get weird when there is no company.

A big plus to working at a company is that things like health insurance, sick days, and 401ks are often taken care of for you. You don’t have to think about them too much because there is generally an HR department getting that all organized for you. You will need things like health insurance when you’re a freelancer, the difference is you’ll need to take care of them for yourself. This means you will have to figure out your own insurance, and manage your own money (cough taxes) on a level you wouldn’t have to at a steady job. This is good because you get to be very financially independent right out the door. The flipside is you will have to learn quickly in order to take proper care of yourself.

9. You will probably work long and strange hours, and you might be tired.

When you freelance you often will get called upon to work strange hours. If you can choose when you work, you might find yourself making final tweaks in the wee hours of the morning. In film and television especially you will work at weird times in strange locations. Also, it’s important to keep in mind that often a freelancer’s day is longer than a regular eight-hour workday, because you need to get more stuff done in a shorter amount of time. The result is you’ll often work 12-16 hour workdays a couple of days in a row and be totally tired when the day is done. This makes simple tasks like swinging by your friend’s party after work seems almost Herculean. Once upon a time one of my best friends threw an Alfred Hitchcock themed party when I was in the middle of working on a particularly intense job, and I literally fell asleep in the middle of her living room floor in front of 20 of our friends. It was 8:30 p.m.. I was that tired.


10. It’s not for everyone.

The biggest thing I would say about freelancing is that it really is not for everyone. I got into it because it seemed like a great way to gain experience in my area of interest. But there really are pros and cons. Freelancing lends itself to the kind of person who is a go-with-the-flow, free spirit, with lots of energy, and thrives on variety in their daily schedule. The hardest thing for me to realize about freelancing was that I’m not that person. I want to be that person so badly, but she is not me. I need a schedule. I thrive on routine. I need to get enough sleep or I make everyone I encounter miserable. My life is more likely to be on track if I know what I’m doing every day. Inconsistency drains me and makes me anxious. I’m a good example of someone who freelanced but shouldn’t be a freelancer forever. Once I recognized this truth about myself I started to work harder on finding a steady gig where I could build some consistency into my life.

These are all the hard learned lessons I encountered as a freelancer. While I loved freelancing and would not go back and change a thing about my experience, I now realize that there was a lot I didn’t know at the time that could have helped me out had I known it then.